Month: August 2020

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.71574-33-9,4,5-Dimethylthiazol-2-amine hydrochloride,as a common compound, the synthetic route is as follows.,71574-33-9

To a solution of (9S)-2-(2-methylpyridin-4-yl)-7,8,9,10-tetrahydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine (600 mg, 2.253 mmol) in THF (15 mL) were added triethylamine (0.942 mL, 6.76 mmol) and triphosgene (334 mg, 1.126 mmol) at 30 C. and stirred for 1 h. Then 4,5-dimethylthiazol-2-amine hydrochloride (556 mg, 3.38 mmol) was added at 30 C. and reaction was heated at 70 C. for 16 h. The solvent evaporated under reduced pressure, residue diluted with water (40 ml) and extracted with DCM (2¡Á40 ml). The combined organic layer was washed with water, brine, dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to obtain crude compound. The crude mixture was purified by flash column chromatography and prep HPLC to afford (9S)-N-(4,5-dimethylthiazol-2-yl)-2-(2-methylpyridin-4-yl)-8,9-dihydro-6H-5,9-methanopyrido[2,3-b][1,4]diazocine-10(7H)-carboxamide (275 mg, 0.655 mmol, 42% yield) as a pale yellow solid (TLC: 10% MeOH in EtOAc, Rf: 0.3), LCMS (m/z): 421.27 [M+H]+. 1H NMR (400 MHz, CDCl3): delta ppm 14.79 (s, 2H), 8.64 (d, J=5.26 Hz, 2H), 8.02 (s, 1H), 7.64 (dd, J=5.26, 1.53 Hz, 1H), 7.54 (q, J=8.11 Hz, 1H), 4.99 (s, 1H), 3.42-3.18 (m, 3H), 3.12-2.89 (m, 1H), 2.79 (s, 3H), 2.28 (s, 3H), 2.22 (s, 3H), 2.00-1.75 (m, 1H), 1.52-1.35 (m, 2H).

The synthetic route of 71574-33-9 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; BLUM, Charles A.; Caldwell, Richard Dana; Casaubon, Rebecca; Disch, Jeremy S.; Fox, Ryan Michael; Koppetsch, Karsten; Miller, William Henry; NG, Pui Yee; Oalmann, Christopher; Perni, Robert B.; Szczepankiewicz, Bruce G.; White, Brian; US2015/152108; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.72054-60-5,Ethyl 2-amino-5-methylthiazole-4-carboxylate,as a common compound, the synthetic route is as follows.,72054-60-5

General procedure: The solution of acid [11(a-d), 12b] (0.5mmol) and O-(benzotriazol-1-yl)-N,N,N?,N’- tetramethyluronium hexafluorophosphate (0.54mmol) in dry dichloromethane (10mL) and dimethyl aminopyridine (0.1mmol) was added to substituted thiazol-2-amine [2(a-c), 4, or 6] (0.5mmol) at 0C. The reaction mixture was stirred at room temperature for 16-20h. Later the reaction was quenched with water (5.0mL), extracted with dichloromethane (10.0mL¡Á2), and evaporated under reduced pressure. The residue was subjected to silica gel chromatography to give compound [(13a-13o) and (14a-14e)] in good yields

The synthetic route of 72054-60-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Guggilapu, Sravanthi Devi; Guntuku, Lalita; Reddy, T. Srinivasa; Nagarsenkar, Atulya; Sigalapalli, Dilep Kumar; Naidu; Bhargava, Suresh K.; Bathini, Nagendra Babu; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 83 – 95;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7210-73-3,Ethyl 4-methylthiazole-2-carboxylate,as a common compound, the synthetic route is as follows.,7210-73-3

A solution of ethyl 4-methyl-1 ,3-thiazole-2-carboxylate (1120) (208 mg, 1.215 mmol) in ethanol (6.028 ml) was stirred at room temperature under an atmosphere of argon. Hydrazine (0.046 ml, 1.458 mmol) was added and the solution was heated to reflux for 18 hours. The solution was cooled to room temperature and then the solvent was removed under reduced pressure to give a pale yellow coloured solid of desired product in 115 mg. LCMS m/z 157.92 [M+H] (at) 0.41 min (2 min run).

The synthetic route of 7210-73-3 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; GLAXO GROUP LIMITED; DEAN, David Kenneth; MUNOZ-MURIEDAS, Jorge; SIME, Mairi; STEADMAN, Jon Graham Anthony; THEWLIS, Rachel Elizabeth Anne; TRANI, Giancarlo; WALTER, Daryl Simon; WO2010/125102; (2010); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

7210-77-7, Ethyl 2,4-dimethylthiazole-5-carboxylate is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7210-77-7

Example 21 Preparation of 2,4-dimethylthiazole-5-methanol To a suspension of lithium aluminum hydride (563 mg, 14.8 mmol) in diethyl ether (25 mL) at 0 C. was added ethyl-2,4-dimethylthiazole-5-carboxylate (2.5 g, 13.5 mmol) in three portions. The reaction mixture was allowed to stir at 0 C. for 10 min, then at room temperature for 24 h. Ethyl acetate (65 mL) was added very slowly dropwise at 0 C. The reaction mixture was then added slowly to an aqueous solution of potassium sodium tartrate (30% w/v; 20 mL) and stirred for 2 h. The layers were separated and the aqueous layer was re-extracted with ethyl acetate (1*30 mL). The combined organic layers were dried (MgSO4), filtered, evaporated under reduced pressure. The resulting colorless solid was dried under high vacuum to give 2,4-dimethylthiazole-5-methanol (1.7 g, 91% yield). This material was used in a subsequent step without further purification.

The synthetic route of 7210-77-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Fotouhi, Nader; Gillespie, Paul; Guthrie, Robert William; Pietranico-Cole, Sherrie Lynn; Yun, Weiya; US2002/161237; (2002); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

7238-61-1, 2-Bromo-4-methylthiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,7238-61-1

General procedure: (Scheme 1, Method C) 4-aminobenzenesulfonamide (4) (1.00 g, 5.81 mmol), 2- hydroxy-3-methoxybenzaldehyde (1.00 g, 7.00 mmol) in EtOH (29 mL) was heated to reflux for 4 h until reaction is an orange turbid mixture. The reaction mixture was cooled to room temperature before sodium borohydride (0.33 g, 8.71 mmol) was added and stirred for an additional 30 min. A white solid forms after 30 min and is collected by filtration and washed with copious amounts of ethanol, dried under vacuum and used as is in subsequent reactions. 1H NMR (400 MHz, DMSO- d6) delta 7.60-7.27 (m, 2H), 6.75-6.40 (m, 4H), 6.06 (t, J= 7.63 Hz, 1H), 4.18 (s, 2H), and 3.65 (s, 3H); 13C NMR (101 MHz, DMSO) delta 40.37, 55.32, 108.91, 109.42, 109.55, 111.29, 111.40, 121.05, 125.05, 127.49, 129.92, 150.17, 152.36, and 156.94; LC-MS retention time (Method 1): 2.876 min. General procedure: (Step iv) 4-(2-hydroxy-3-methoxybenzylamino)benzenesulfonamide (5) (0.58 mmol), arylbromide (0.70 mmol), K2CO3 (1.45 mmol), N,N’-dimethylethylenediamine (0.29 mmol), and copper(I)iodide (0.03 mmol) in 1,4-dioxane (1.5 mL) were place under N2 and sealed in a 5 mL sealed tube. The reaction was heated to 70 C for 6 to 8 h and monitored by LC/MS analysis. Upon completion the heterogeneous mixture was cooled to room temperature, filtered, and washed with dioxane. The solution was passed through a thiol cartridge (metal scavenging), diluted with AcOEt and washed with NH4CI (2X), water, and brine. The crude material was purified using a prep-HPLC (gradient 10-100% acetonitrile w/ 0.1% TFA in water w/ 0.1% TFA) to give the desired product. 4-(2-hydroxy-3-methoxybenzylamino)- V-(4-methylthiazol-2-yl)benzenesulfonamide TFA (40): Method C: using 2-bromo-4-methylthiazole; 1H NMR (400 MHz, DMSO-<) delta 12.31 (s, 1 H), 8.70 (s, 1 H), 7.48-7.32 (m, 3 H), 6.89-6.72 (m, 6 H), 6.61-6.47 (m, 3 H), 6.27 (s, 1 H), 4.20 (d, J= 5.90 Hz, 2 H), 3.76 (s, 3 H), and 1.95 (s, 3 H); LC-MS retention time (Method 1): 1.962 min; HRMS: m/z (M+H)+ (Calculated for C18H20N3O4S2, 406.0890) found 406.0875. The synthetic route of 7238-61-1 has been constantly updated, and we look forward to future research findings. Reference£º
Patent; EASTERN VIRGINIA MEDICAL SCHOOL; MALONEY, David, J.; LUCI, Diane, K.; JADHAV, Ajit; HOLMAN, Theodore; NADLER, Jerry, L.; HOLINSTAT, Michael; TAYLOR-FISHWICK, David; SIMEONOV, Anton; YASGAR, Adam; WO2015/54662; (2015); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

74370-93-7, 4-(tert-Butyl)thiazol-2-amine is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,74370-93-7

Into a Vial was added the 6-Chloro-pyridine-3-sulfonic thiazol-2-ylamide (35 mg, 0.00013 mol), Sodium tert-butoxide (36 mg, 0.00038 mol), 9,9-DIMETHYL-4,5-BIS(DIPHENYLPHOSPHINO)XANTHENE (8.8 mg, 0.000015 mol), Tris(dibenzylideneacetone)dipalladium(0) (4.6 mg, 0.0000051 mol), 2-AMINO-4-(4-CHLOROPHENYL)THIAZOLE and the de-gased anhydrous 1,4-Dioxane (1.7 mL, 0.022 mol). The reaction mixture was heated at 150 C. for 1 h in microwave. The reaction mixture was filtered through celite and the filtrate was concentrated to give the crude product that was purified on Gilson (semi-prep, reverse phase, Phenomenex 100¡Á21.2 mm 10 micron C18 column, 20 mL/min, Gradient 85% A to 100% B over 25 min. Solvent A: 7800 water/200 acetonitrile/8 TFA. Solvent B: 7200 acetonitrile/800 water/8 TFA). Fractions were checked by LC/MS and then dried on a lyophilizer to give the desired product as TFA salt (yellow powder).

The synthetic route of 74370-93-7 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Icagen; US2009/23740; (2009); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.74537-49-8,2-(Methylthio)benzo[d]thiazol-6-ol,as a common compound, the synthetic route is as follows.,74537-49-8

Step 1. Preparation of 6-(2-chloropyridin-4-yloxy)-2-(methylthio)benzo[d]thiazole To the mixture of 2-(methylthio)benzo[d]thiazol-6-ol (1 g, 5.08 mmol) and cesium carbonate (4.55 g, 14 mmol) in 15 ml of NMP was added 2-chloro-4-fluoropyridine (1.32 mg, 10 mmol). The reaction mixture was stirred at 55 C. for overnight. The reaction mixture was poured into 80 ml of aq. saturated NaHCO3 and extracted with ethyl acetate (2*150 ml). The combined organic layers were washed with aq. 0.1M NaHSO4 (60 ml), water (2*60 ml) and brine (60 ml), then dried over MgSO4, filtered and evaporated in vacuo to give 6-(2-chloropyridin-4-yloxy)-2-(methylthio)benzo[d]thiazole (1.72 g) as brown oil that carried on to next step without purification. ES/MS m/z 308.9 (MH+).

The synthetic route of 74537-49-8 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Novartis AG; US2008/45528; (2008); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

768-11-6, 5-Bromobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,768-11-6

At room temperature, the iodobenzene (0.4mmol, 1 equiv), selenium (1.2mmol, 3 equiv), 5 – bromo and thiazole (0.8mmol, 2 equiv), CuO (0.04mmol), cesium carbonate (1.2mmol, 3 equiv) is added to the reaction tube, and then the nitrogen, and replace the three times, the reaction environment under nitrogen, then adding the reaction solvent 2 ml DMI, in the 140 C the reaction temperature under stirring 24h. By thin-layer chromatographic monitoring after the reaction, the reaction mixture is cooled, then adding ethyl acetate dilution, the diluted solution in the transfer to the separatory funnel, saturated salt water for extraction, the aqueous phase and the organic phase separated, then the ethyl acetate extract the aqueous phase 3 times, merge all organic phase (namely the saturated salt water extraction and separation of the organic phase and the ethyl acetate extraction and separation of the organic phase), adding 5g anhydrous sodium sulfate, stirring 5 minutes after the filtering, the filter cake washing 3 times, for each time 5 ml ethyl acetate wash, then evaporate the solvent, column chromatography (petroleum ether and ethyl ether volume ratio 100:1 mixture as eluant, silica gel as 300 – 400 mesh silica gel) product is obtained after the 5 – bromo -2 – (benzene selenium) benzothiazole, white solid, yield 88%.

The synthetic route of 768-11-6 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Wenzhou University; Liu, Miaocheng; Gao, Chao; Gao, Wenxia; Chen, Jiuxi; Huang, Xiaobo; Wu, Huayue; (16 pag.)CN106565629; (2017); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

769-20-0, 6-Amino-7-bromobenzothiazole is a thiazole compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated,769-20-0

Example 30; 7-Bromo-benzothiazoleSodium nitrite (0.229 g, 3.3 mmol) was added to a solution of 7-bromo-benzothiazol-6-ylamine (0.380 g, 1.66 mmol, described in WO 97/31636) in sulfuric acid (10 mL) and the resulting mixture was stirred at room temperature for 20 min. Hypophosphorous acid (10 mL) was added and the mixture was heated at 50 C. overnight. The pH was adjusted to 9-10 by addition of sodium carbonate, and the crude product was removed by filtration and washed with water. Purification by prep-HPLC gave 0.265 g (75% yield) of the title compound as a white solid: LC-MS (EI) m/z 213 (M++1).

The synthetic route of 769-20-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; AstraZeneca AB; US2011/98292; (2011); A1;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.7709-58-2,4-(Chloromethyl)thiazole hydrochloride,as a common compound, the synthetic route is as follows.,7709-58-2

Reference Example 5 6,7,8-Trifluoro-1-(4-thiazolylmethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid 1.5 g of ethyl 6,7,8-trifluoro-4-hydroxyquinoline-3-carboxylate was dissolved in 30 ml of DMF, and 0.43 g of 60% oily sodium hydride was added, followed by stirring at 80 C. in a nitrogen gas stream for 20 minutes. To this solution, 1.9 g of 4-chloromethylthiazole hydrochloride was added, followed by stirring at constant temperature for 15 hours, after which the reaction mixture was concentrated to dryness. The residue was dissolved in CHCl3; the organic layer was washed with water and dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate=1:2) to yield 0.46 g of ethyl 6,7,8-trifluoro-1-(4-thiazolylmethyl)-1,4-dihydro-4-oxoquinoline-3-carboxylate as a colorless powder.

The synthetic route of 7709-58-2 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; Takeda Chemical Industries, Ltd.; US5519024; (1996); A;,
Thiazole | C3H3NS – PubChem
Thiazole | chemical compound | Britannica